EP2535958B1 - Élément électroluminescent organique - Google Patents

Élément électroluminescent organique Download PDF

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EP2535958B1
EP2535958B1 EP20110742195 EP11742195A EP2535958B1 EP 2535958 B1 EP2535958 B1 EP 2535958B1 EP 20110742195 EP20110742195 EP 20110742195 EP 11742195 A EP11742195 A EP 11742195A EP 2535958 B1 EP2535958 B1 EP 2535958B1
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carbon atoms
organic
layer
formula
light
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EP2535958A4 (fr
EP2535958A1 (fr
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Takahiro Kai
Masaki Komori
Toshihiro Yamamoto
Megumi Matsumoto
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Nippon Steel Chemical and Materials Co Ltd
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Nippon Steel and Sumikin Chemical Co Ltd
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
    • C07D487/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms

Definitions

  • This invention relates to an organic electroluminescent device containing an indolocarbazole compound and, more particularly, to a thin film type device that emits light upon application of an electric field to a light-emitting layer composed of an organic compound.
  • organic electroluminescent device in the simplest structure is generally constituted of a light-emitting layer and a pair of counter electrodes holding the light-emitting layer between them.
  • the organic EL device functions by utilizing the following phenomenon; upon application of an electric field between the electrodes, electrons are injected from the cathode and holes are injected from the anode and they recombine in the light-emitting layer with emission of light.
  • the aforementioned device comprising a hole-transporting layer composed of an aromatic diamine and a light-emitting layer composed of Alq3 and many others have utilized fluorescence.
  • the utilization of phosphorescence that is, emission of light from the triplet excited state, is expected to enhance the luminous efficiency three to four times that of the conventional devices utilizing fluorescence (emission of light from the singlet excited state).
  • the use of coumarin derivatives and benzophenone derivatives in the light-emitting layer was investigated, but these derivatives merely produced luminance at an extremely low level.
  • Patent document 1 JP 2003-515897 A
  • Patent document 2 JP 2001-313178 A
  • Patent document 3 JP 4388590
  • Patent document 4 WO 2009-148015
  • Patent document 5 JP 2006-193729 A
  • CBP 4,4'-bis(9-carbazolyl)biphenyl
  • Ir(ppy) 3 tris(2-phenylpyridine)iridium complex
  • an organic EL device In order for an organic EL device to display high luminous efficiency, a host material that has high triplet excitation energy and is well balanced in the injection and transportation characteristics of electric charges (holes and electrons) is required. Furthermore, compounds that are electrochemically stable, highly resistant to heat, and excellently stable in the amorphous state are desired and further improvements are demanded.
  • Patent document 3 discloses the compound illustrated below as a host material.
  • Patent document 4 discloses the compound illustrated below as a host material.
  • the said document discloses a compound in which five-membered chalcogen-containing rings and six-membered aromatic hydrocarbon rings are alternately fused together.
  • the document does not concretely disclose a compound in which five-membered nitrogen-containing rings and six-membered aromatic hydrocarbon rings are alternately fused together in a combined total of 7 rings or more and by no means discloses the usefulness of such a compound.
  • patent document 5 discloses the compound illustrated below.
  • an object of this invention is to provide an organic EL device exhibiting such luminous efficiency and driving stability as to be practically useful and to provide a compound suitable therefor.
  • the inventors of this invention have conducted intensive studies, found that the use of an indolocarbazole compound composed of nitrogen-containing aromatic heterocyclic rings and aromatic hydrocarbon linking groups in an organic EL device enables the device to display excellent characteristics, and completed this invention.
  • This invention relates to an organic electroluminescent device comprising an anode, organic layers containing a phosphorescent light-emitting layer, and a cathode piled one upon another on a substrate wherein at least one organic layer selected from the group consisting of a light-emitting layer, a hole-transporting layer, an electron-transporting layer, a hole-blocking layer, and an electron-blocking layer contains a compound represented by general formula (1).
  • Z is a group formed from a compound represented by formula (1a) by removing one of Ars possessed by the said compound;
  • L is an aromatic hydrocarbon group of 6 to 50 carbon atoms or an aromatic heterocyclic group of 3 to 50 carbon atoms;
  • m is an integer of 1 to 4 and, when m is 2 or more, Zs may be identical with or different from one another.
  • ring A is a hydrocarbon ring represented by formula (1b) and fused to the adjacent rings at arbitrary positions
  • ring B is a heterocyclic ring represented by formula (1c) and fused to the adjacent rings at arbitrary positions
  • n is an integer of 2 to 4.
  • each of a plurality of Rs is independently a hydrogen atom, an aliphatic hydrocarbon group of 1 to 10 carbon atoms, an aromatic hydrocarbon group of 6 to 18 carbon atoms, or an aromatic heterocyclic group of 3 to 17 carbon atoms.
  • each of a plurality of Ars is independently an aromatic hydrocarbon group of 6 to 50 carbon atoms or an aromatic heterocyclic group of 3 to 50 carbon atoms; however, at least one of L and a plurality of Ars is an m-valent or monovalent group formed from a compound represented by formula (1d) by removing hydrogen atoms or a hydrogen atom.
  • X is a methine group, a nitrogen atom, or C-Ar 1 and at least one of Xs is a nitrogen atom; each Ar 1 is independently an aromatic hydrocarbon group of 6 to 50 carbon atoms or an aromatic heterocyclic group of 3 to 50 carbon atoms.
  • n is preferably 2.
  • formula (1a) is preferably represented by any one of formulas (2) to (4) shown below.
  • the organic layer containing the aforementioned compound is a light-emitting layer containing a phosphorescent dopant.
  • a compound represented by general formula (1) has a configuration in which five-membered nitrogen-containing rings and six-membered aromatic hydrocarbon rings are alternately fused together in a combined total of 7 rings or more. It is conceivable that the use of this compound in an organic EL device enables the device to display good injection and transportation characteristics of holes and electrons and have high durability. An organic EL device using this compound functions at low driving voltage. Particularly, in the case where the compound is incorporated in the light-emitting layer, the balance of electric charges in the device improves and, as a result, the probability of recombination improves.
  • the compound has high energy in the lowest excited triplet state and can suppress transfer of the triplet excitation energy from the dopant to the host molecule and this characteristic is likely to provide excellent luminous characteristics.
  • the compound exhibits a good property in the amorphous state and high thermal stability and is electrochemically stable and these properties conceivably contribute to realize organic EL devices of long driving life and high durability.
  • Fig. 1 shows an example of the structure of an organic EL device.
  • An organic electroluminescent device contains a compound represented by the aforementioned general formula (1). That is, as shown by formula (1a), the compound has a skeleton formed by additionally fusing 1 to 3 indole rings in series to the indolocarbazole ring. Further, the compound has at least one non-fused nitrogen-containing heterocyclic ring on a nitrogen atom in the aforementioned skeleton.
  • L is an m-valent aromatic hydrocarbon group of 6 to 50 carbon atoms or an m-valent aromatic heterocyclic group of 3 to 50 carbon atoms; preferably an m-valent aromatic hydrocarbon group of 6 to 18 carbon atoms or an m-valent aromatic heterocyclic group of 3 to 18 carbon atoms.
  • aromatic hydrocarbon group and the aromatic heterocyclic group include groups formed by removing a hydrogen atom or hydrogen atoms from benzene, pentalene, indene, naphthalene, azulene, heptalene, octalene, indacene, acenaphthylene, phenalene, phenanthrene, anthracene, trindene, fluoranthene, acephenanthrylene, aceanthrylene, triphenylene, pyrene, chrysene, tetraphene, tetracene, pleiadene, picene, perylene, pentaphene, pentacene, tetraphenylene, cholanthrylene, helicene, hexaphene, rubicene, coronene, trinaphthylene, heptaphene, pyranthrene, ovalene, corann
  • the number of linked aromatic rings is preferably 2 to 10, more preferably 2 to 7, and the aromatic rings to be linked may be identical with or different from one another.
  • the position of linkage of L to N in the ring represented by formula (1a) is not limited and the linkage may occur in the ring at the end or in the middle of the linked rings.
  • the "aromatic ring” here is used as a general term to cover both the aromatic hydrocarbon ring and the aromatic heterocyclic ring.
  • Specific examples of the aforementioned groups formed from the aromatic compounds in which a plurality of aromatic rings are linked together include groups formed by removing a hydrogen atom or hydrogen atoms from biphenyl, terphenyl, bipyridine, bipyrimidine, bitriazine, terpyridine, bistriazylbenzene, dicarbazolylbenzene, carbazolylbiphenyl, dicarbazolylbiphenyl, indolocarbazolyltriazine, phenylterphenyl, carbazolylterphenyl, binaphthalene, phenylpyridine, phenylcarbazole, diphenylcarbazole, diphenylpyridine, phenylpyrimidine, diphenylpyrimidine, phenyltriazine, diphenyltriazine, phenylnaphthalene, diphenylnaphthalene, indolocarbazolylbenzene, indolocarbazol
  • the aforementioned aromatic rings may have a substituent.
  • the aromatic rings have a substituent
  • preferable examples of the substituent include an alkyl group of 1 to 4 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, an alkoxyl group of 1 to 2 carbon atoms, an acetyl group, and a diarylamino group of 6 to 24 carbon atoms.
  • a plurality of substituents may be identical with or different from one another.
  • the number of carbon atoms in the substituents is included in counting the total number of carbon atoms in the aforementioned aromatic rings having substituents.
  • Z is a group formed by removing one of Ars from a compound represented by formula (1a).
  • ring A is a hydrocarbon ring represented by formula (1b) and fused to the adjacent rings and ring B is a heterocyclic ring represented by formula (1c) and fused to the adjacent rings.
  • the hydrocarbon ring represented by formula (1b) may be fused to the adjacent rings at arbitrary positions, the number of positions where fusion can occur is structurally limited. That is, this hydrocarbon ring has 6 sides, but two adjacent sides in the ring cannot be fused respectively to the two adjacent rings.
  • the heterocyclic ring represented by formula (1c) may be fused to the adjacent rings at arbitrary positions, but here again the position where fusion can occur is structurally limited.
  • This heterocyclic ring has five sides, but two adjacent sides cannot be fused respectively to the two adjacent rings nor the side containing N can be fused to the adjacent ring. Therefore, the number of skeletons of the compound represented by formula (1a) is limited, but this number increases as n increases.
  • n is an integer of 2 to 4, preferably 2 or 3, more preferably 2.
  • n number of ring As or ring Bs may be identical with or different from one another.
  • the positions of fusion of ring A to ring B may be identical with or different from one another.
  • each R is independently a hydrogen atom, an aliphatic hydrocarbon group of 1 to 10 carbon atoms, an aromatic hydrocarbon group of 6 to 18 carbon atoms, or an aromatic heterocyclic group of 3 to 17 carbon atoms; preferably, a hydrogen atom, an aliphatic hydrocarbon group of 1 to 6 carbon atoms, a phenyl group, a pyridyl group, a pyrimidyl group, or a triazyl group; more preferably, a hydrogen atom, a phenyl group, a pyridyl group, a pyrimidyl group, or a triazyl group.
  • each Ar is independently an aromatic hydrocarbon group of 6 to 50 carbon atoms or an aromatic heterocyclic group of 3 to 50 carbon atoms, preferably an aromatic hydrocarbon group of 6 to 18 carbon atoms, an aromatic heterocyclic group of 3 to 18 carbon atoms, or an aromatic compound in which a plurality of these aromatic rings are linked together. In the case where a plurality of aromatic rings are linked together, the total number of carbon atoms is 6 to 50.
  • Specific examples of the aromatic hydrocarbon group or aromatic heterocyclic group are the same as those for of L where L is a monovalent group.
  • At least one of L and Ars is an m-valent or monovalent group derived from a compound represented by formula (1d).
  • X is a methine group, a nitrogen atom, or C-Ar 1 and at least one of Xs is a nitrogen atom.
  • L or Ar is an m-valent or monovalent group
  • the m number of methine groups or a methine group represent the m number of carbon atoms or a carbon atom remaining after removal of the m number of hydrogen atoms or a hydrogen atom.
  • the total number of nitrogen atoms is preferably an integer of 1 to 4, more preferably an integer of 1 to 3.
  • m + number of nitrogen atoms is 6 or less.
  • the total number of C-Ar 1 s is preferably an integer of 1 to 3, more preferably 1 or 2.
  • each Ar 1 is independently an aromatic hydrocarbon group of 6 to 50 carbon atoms or an aromatic heterocyclic group of 3 to 50 carbon atoms, preferably an aromatic hydrocarbon group of 6 to 18 carbon atoms, an aromatic heterocyclic group of 3 to 18 carbon atoms, or an aromatic compound in which a plurality of these aromatic rings are linked together. In the case where a plurality of aromatic rings are linked together, the total number of carbon atoms is 6 to 50.
  • Specific examples of the aromatic hydrocarbon group or aromatic heterocyclic group are the same as those for of L where L is a monovalent group.
  • m is an integer of 1 to 4, preferably an integer of 1 to 3, more preferably 1 or 2.
  • n and the positions of fusion of ring A to ring B may be identical in each case or differ from case to case.
  • the indolocarbazole compounds represented by general formula (1) can be synthesized by selecting raw materials according to the structure of the target compound and using a known technique.
  • the diindolo[2,3-a:3',2'-i]carbazole skeleton (A), the diindolo[2,3-a:2',3'-h]carbazole skeleton (B), and the diindolo[3,2-b:2',3'-h]carbazole skeleton (C) can respectively be synthesized by the reaction formulas shown below with reference to synthetic examples described in The Journal of Organic Chemistry, 2004, Vol. 69 (17), 5705 and Organic Letters, 2004, Vol. 6, No. 19, 3413 .
  • an organic EL device comprises an anode, a plurality of organic layers, and a cathode piled one upon another on a substrate, incorporation of a compound represented by general formula (1) in at least one of the organic layers helps provide an excellent organic EL device.
  • An organic layer suitable for this purpose is a light-emitting layer, an electron-transporting layer, a hole-blocking layer, or an electron-blocking layer.
  • the compound is incorporated as a host material in a light-emitting layer containing a phosphorescent dopant.
  • the organic EL device of this invention comprises organic layers at least one of which contains a light-emitting layer disposed between an anode and a cathode piled one upon another on a substrate and, further, at least one organic layer selected from a light-emitting layer, an electron-transporting layer, a hole-blocking layer, and an electron-blocking layer contains a compound represented by general formula (1).
  • the light-emitting layer contains a compound represented by general formula (1) together with a phosphorescent dopant.
  • Fig. 1 is the cross section to illustrate an example of the structure of an organic EL device generally used in this invention and the numbers in the figure stand for the following: 1 for a substrate, 2 for an anode, 3 for a hole-injecting layer, 4 for a hole-transporting layer, 5 for a light-emitting layer, 6 for an electron-transporting layer, and 7 for a cathode.
  • the organic EL device of this invention may further comprise an exciton-blocking layer adjacent to the light-emitting layer or an electron-blocking layer between the light-emitting layer and the hole-injecting layer.
  • the exciton-blocking layer may be inserted either on the anode side or on the cathode side of the light-emitting layer or may be inserted simultaneously on both sides.
  • the organic EL device of this invention comprises the substrate, the anode, the light-emitting layer, and the cathode as essential layers.
  • the device comprises a hole-injecting/transporting layer and an electron-injecting/transporting layer in addition to the essential layers and further comprises a hole-blocking layer between the light-emitting layer and the electron-injecting/transporting layer.
  • the hole-injecting/transporting layer means a hole-injecting layer and/or a hole-transporting layer while the electron-injecting/transporting layer means an electron-injecting layer and/or an electron-transporting layer.
  • the organic EL device of this invention can be so constructed as to have a structure that is the reverse of the structure illustrated in Fig. 1 by piling the cathode 7, the electron-transporting layer 6, the light-emitting layer 5, the hole-transporting layer 4, and the anode 2 one upon another in this order on the substrate 1. In this case, it is also possible to add or omit a layer or layers according to the need.
  • the organic EL device of this invention is preferably supported by a substrate.
  • a substrate There is no specific restriction on the substrate and any of the substrates which have been used customarily in organic EL devices can be used.
  • a substrate made from glass, transparent plastic, or quartz may be used.
  • the anode of an organic EL device is preferably made from an electrode substance having a high work function (4 eV or more) such as a metal, an alloy, an electrically conductive compound, and a mixture thereof.
  • the electrode substances of this kind include metals such as Au and electrically conductive transparent materials such as CuI, indium tin oxide (ITO), SnO 2 , and ZnO.
  • a material that is amorphous and formable into a transparent electrically conductive film such as IDIXO (In 2 O 3 -ZnO) may be used.
  • the anode may be formed by preparing a thin film from any of those electrode substances by a method such as vapor deposition and sputtering and then forming a pattern of desired shape on the thin film by photolithography. Or, in the case where high accuracy is not required in patterning (100 ⁇ m or more), a pattern may be formed through a mask of desired shape during vapor deposition or sputtering of the aforementioned electrode substance. In the case where a substance that is applicable by a coating method such as an electrically conductive organic compound is used, a wet film-forming process such as printing and coating may be employed.
  • the transmittance is desirably set at 10% or more and the sheet resistance as the anode is preferably several hundred ⁇ / ⁇ or less.
  • the thickness of the film is normally selected from the range of 10 to 1,000 nm, preferably 10 to 200 nm, although it varies with the film-forming material.
  • the cathode is made from an electrode substance having a low work function (4 eV or less) such as a metal (hereinafter referred to as electron-injecting metal), an alloy, an electrically conductive compound, and a mixture thereof.
  • a metal hereinafter referred to as electron-injecting metal
  • the electrode substances of this kind include sodium, a sodium-potassium alloy, magnesium, lithium, a magnesium/copper mixture, a magnesium/silver mixture, a magnesium/aluminum mixture, a magnesium/indium mixture, an aluminum/aluminum oxide (Al 2 O 3 ) mixture, indium, a lithium/aluminum mixture, and a rare earth metal.
  • a mixture of an electron-injecting metal and a second metal that is higher in work function and more stable than the electron-injecting metal is suitable for use as an electrode substance and examples thereof include a magnesium/silver mixture, a magnesium/aluminum mixture, a magnesium/indium mixture, an aluminum/aluminum oxide (Al 2 O 3 ) mixture, a lithium/aluminum mixture, and aluminum.
  • the cathode is formed by preparing a thin film from any of those electrode substances by a method such as vapor deposition and sputtering.
  • the sheet resistance as the cathode is preferably several hundred ⁇ / ⁇ or less and the thickness of the film is selected from the range of 10 nm to 5 ⁇ m, preferably 50 to 200 nm.
  • Making either the anode or the cathode of an organic EL device transparent or translucent in order to transmit emitted light advantageously improves the luminance.
  • a transparent or translucent cathode may be made by forming a cathode with a film thickness of 1 to 20 nm from the aforementioned metal and then forming thereon a film of one of the electrically conductive transparent materials described above in explanation of the anode. This method can be applied to fabricate a device in which both the anode and the cathode display good transmittance properties.
  • the light-emitting layer is a phosphorescent light-emitting layer and contains a phosphorescent dopant and a host material.
  • the phosphorescent dopant include an organic metal complex containing at least one metal selected from ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum, and gold.
  • the organic metal complexes of this kind are known in the aforementioned prior art technical documents and elsewhere and a suitable organic metal complex may be selected from them and used.
  • the phosphorescent dopant include a complex containing a noble metal element such as Ir in the center, typically Ir(ppy) 3 , a complex such as (Bt) 2 Iracac, and a complex such as (Btp)Ptacac. Specific examples of these complexes are illustrated below, but the complexes useful for this invention are not limited thereto.
  • the content of the aforementioned phosphorescent dopant in the light-emitting layer is preferably in the range of 1 to 50 wt%, more preferably 5 to 30 wt%.
  • a compound represented by the aforementioned general formula (1) is preferable to use as a host material in the light-emitting layer.
  • a host material other than the said compound may be used in the light-emitting layer.
  • the said compound may be used together with other host material.
  • plural kinds of known host materials may be used together.
  • the ones suitable for use preferably have a hole transport ability and an electron transport ability, can prevent the wavelength of emitted light from shifting to longer wavelengths, and have a high glass transition temperature.
  • Such known host materials are described in a large number of patent documents and elsewhere and a suitable material may be selected from them.
  • Specific examples include, but are not limited to, indole derivatives, carbazole derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aromatic tertiary amine compounds, styrylamine compounds, aromatic dimethylidene-based compounds, porphyrin-based compounds, anthraquinodimethan derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, heterocyclic t
  • the injecting layer is a layer which is provided between an electrode and an organic layer to reduce the driving voltage and improve the luminance.
  • the injecting layer includes a hole-injecting layer and an electron-injecting layer and may be provided respectively between the anode and the light-emitting layer or the hole-transporting layer and between the cathode and the light-emitting layer or the electron-transporting layer.
  • the injecting layer may be provided according to the need.
  • the hole-blocking layer has a function of the electron-transporting layer in a broad sense and is composed of a hole-blocking material that has an extremely poor ability to transport holes while having a function of transporting electrons.
  • the hole-blocking layer can improve the probability of recombination of electrons and holes by transporting electrons while blocking holes.
  • a compound represented by general formula (1) in the hole-blocking layer.
  • a known hole-blocking material may be used instead.
  • any one of the materials for the electron-transport.ing layer to be described later on may be used as a hole-blocking material according to the need.
  • the electron-blocking layer is composed of a material that has an extremely poor ability to transport electrons while having a function of transporting holes and it can improve the probability of recombination of electrons and holes by transporting holes while blocking electrons.
  • the electron-blocking layer it is preferable to use a compound represented by general formula (1) in the electron-blocking layer.
  • a known electron-blocking material may be used instead.
  • As a material for the electron-blocking layer any one of the materials for the hole-transporting layer to be described later on may be used according to the need.
  • the thickness of the electron-blocking layer is preferably 3 to 100 nm, more preferably 5 to 30 nm.
  • the exciton-blocking layer is a layer for blocking excitons that are generated by the recombination of holes and electrons in the light-emitting layer from diffusing to the charge-transporting layer.
  • the insertion of this layer makes it possible to efficiently confine excitons in the light-emitting layer and enhance the luminous efficiency of the device.
  • the exciton-blocking layer may be inserted either on the anode side or on the cathode side adjacent to the light-emitting layer or simultaneously on both the anode and the cathode sides.
  • Examples of a material for the exciton-blocking layer include 1,3-dicarbazolylbenzene (mCP) and bis(2-methyl-8-quinolinolato)-4-phenylphenolatoaluminum(III) (BAlq).
  • the hole-transporting layer is composed of a hole-transporting material that has a function of transporting holes and it may be provided in a single layer or a plurality of layers.
  • the hole-transporting material has either a property of injecting or transporting holes or a property of constituting a barrier to electrons and it may be either an organic substance or an inorganic substance.
  • a compound represented by general formula (1) in the hole-transporting layer a suitable compound is selected from known compounds and used.
  • hole-transporting materials suitable for use include triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline-based copolymers, and electrically conductive oligomers, particularly thiophene oligomers.
  • Preferable examples include porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds and more preferable examples include aromatic tertiary amine compounds.
  • the electron-transporting layer is composed of a material that has a function of transporting electrons and may be provided in a single layer or a plurality of layers.
  • An electron-transporting material may be an arbitrary material so long as it has a function of transporting electrons that are injected from the cathode to the light-emitting layer. It is preferable to use a compound represented by general formula (1) in the electron-transporting layer, but an arbitrary material may be selected from the known compounds and used. Examples of such known compounds include nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimide, fluorenylidenemethane derivatives, anthraquinodimethan derivatives, anthrone derivatives, and oxadiazole derivatives.
  • thiadiazole derivatives that are derived from the aforementioned oxadiazole derivatives by substituting a sulfur atom for the oxygen atom of the oxadiazole ring and quinoxaline derivatives that have a quinoxaline ring known as an electron-withdrawing group may be used as electron-transporting materials.
  • polymer materials that contain any of these materials in the polymer chain or polymer materials whose backbone is constituted of any of these materials may be used.
  • the constituent layers were deposited in thin film by the vacuum deposition process at a degree of vacuum of 4.0 ⁇ 10 -5 Pa one upon another on a glass substrate on which a 110 nm-thick ITO anode had been formed.
  • copper phthalocyanine (CuPC) was deposited on the ITO anode to a thickness of 25 nm.
  • NPB 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl
  • lithium fluoride LiF
  • aluminum Al was deposited as an electrode on the electron-injecting layer to a thickness of 70 nm to finish the fabrication of an organic EL device.
  • An organic EL device was fabricated as in Example 1 except that 4,4'-bis(9-carbazolyl)biphenyl (CBP) was used as the host material in the light-emitting layer.
  • CBP 4,4'-bis(9-carbazolyl)biphenyl
  • An organic EL device was fabricated as in Example 1 except that Compound H-1 shown below was used as the host material in the light-emitting layer.
  • Example 1 Each of the organic EL devices fabricated in Example 1 and Comparative Examples 1 and 2 was connected to an external power source and, when direct current voltage was applied, the device was confirmed to have the luminous characteristics shown in Table 1.
  • Table 1 the headword "compound” denotes the compound used as a host material and the values of the luminance, voltage, and luminous efficiency are obtained when the device was driven at 10 mA/cm 2 .
  • the peak emission wavelength of each device is 530 nm and this proves that light is emitted from Ir(ppy) 3 .
  • Table 1 Compound Luminance (cd/m 2 ) Voltage (V) Luminous efficiency (1m/W) Example 1 1 2970 6.7 13.9 Comparative Example 1 CBP 2420 9.3 8.2 2 H-1 2840 7.4 12.1
  • the constituent layers were deposited in thin film by the vacuum deposition process at a degree of vacuum of 4.0 ⁇ 10 -4 Pa one upon another on a glass substrate on which a 150 nm-thick ITO anode had been formed.
  • copper phthalocyanine (CuPC) was deposited on the ITO anode to a thickness of 25 nm to form a hole-injecting layer.
  • NPB was deposited on the hole-injecting layer to a thickness of 55 nm to form a hole-transporting layer.
  • Compound 24 as a host material and bis(2-(2'-benzo[4,5-a]thienyl)pyridinato-N,C3]iridium(acetylacetonate) ((Btp) 2 Iracac) were co-deposited on the hole-transporting layer from different deposition sources to a thickness of 47.5 nm to form a light-emitting layer. At this time, the concentration of (Btp) 2 Iracac was 8.0 wt%.
  • Alq3 was deposited to a thickness of 30 nm to form an electron-transporting layer. Further, LiF was deposited on the electron-transporting layer to a thickness of 1 nm to form an electron-injecting layer.
  • Al was deposited as an electrode on the electron-injecting layer to a thickness of 200 nm to finish the fabrication of an organic EL device.
  • An organic EL device was fabricated as in Example 2 except that Compound 31 was used as the host material in the light-emitting layer.
  • An organic EL device was fabricated as in Example 2 except that bis(2-methyl-8-quinolinolato)-4-phenylphenolatoaluminum(III) (BAlq) was used as the host material in the light-emitting layer.
  • BAlq bis(2-methyl-8-quinolinolato)-4-phenylphenolatoaluminum(III)
  • An organic EL device was fabricated as in Example 2 except that Compound H-1 was used as the host material in the light-emitting layer.
  • each of the organic EL devices fabricated in Examples 2 and 3 and Comparative Examples 3 and 4 was connected to an external power source and, when direct current voltage was applied, the device was confirmed to have the luminous characteristics shown in Table 2.
  • Table 2 the values of the luminance, voltage, and luminous efficiency are obtained when the device was driven at 10 mA/cm 2 .
  • the peak emission wavelength of each device is 620 nm and this proves that light is emitted from (Btp) 2 Iracac.
  • Table 2 Compound Luminance (cd/m 2 ) Voltage (V) Luminous efficiency (lm/W)
  • An organic EL device having a structure formed by omitting the hole-transporting layer from and adding an electron-injecting layer to the structure shown in Fig. 1 was fabricated.
  • a glass substrate on which a 150 nm-thick ITO anode had been formed was submitted to UV ozone cleaning and drying.
  • a 20 wt% ethanol solution of PEDOT ⁇ PSS (Baytron P CH8000) was applied to the ITO anode on the glass substrate by spin coating at 3,000 rpm for 60 seconds and dried at 200°C for 60 minutes to form a hole-injecting layer. At this time, the thickness of the hole-injecting layer was 25 nm.
  • An organic EL device was fabricated as in Example 3 except that Compound 35 was used as the host material in the light-emitting layer.
  • An organic EL device was fabricated as in Example 3 except that Compound H-1 was used as the host material in the light-emitting layer.
  • the organic EL device of this invention satisfies a level of performance required for practical use with respect to the luminous characteristics, driving life, and durability and is of high technical value because of its potential applicability to flat panel displays (cellular phone display devices, vehicle-mounted display devices, office computer display devices, and television sets), light sources utilizing the characteristics of planar light emitters (illumination, light sources for copying machines, and backlight sources for liquid crystal displays and meters), display boards, and marker lamps.

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Claims (5)

  1. Dispositif électroluminescent organique comprenant une anode, des couches organiques contenant une couche émettant une lumière phosphorescente, et une cathode, empilées les unes sur les autres sur un substrat, dans lequel au moins une couche organique choisie dans l'ensemble constitué par une couche luminescente, une couche de transport de trous, une couche de transport d'électrons, une couche de blocage de trous, et une couche de blocage d'électrons, contient un composé représenté par la formule générale (1) :
    Figure imgb0059
    Figure imgb0060
    Figure imgb0061
     dans la formule générale (1), Z est un groupe monovalent formé par retrait de l'un des Ar sur un composé représenté par la formule (1a) ; L est un groupe hydrocarboné aromatique m-valent possédant de 6 à 50 atomes de carbone ou un groupe hétérocyclique aromatique m-valent possédant de 3 à 50 atomes de carbone ; m est un entier de 1 à 4 et, quand m vaut 2 ou plus, les Z peuvent être identiques ou différents ;
    dans la formule (1a), le cycle A est un cycle hydrocarboné représenté par la formule (1b) et fusionné aux cycles adjacents en des positions arbitraires, le cycle B est un hétérocycle représenté par la formule (1c) et fusionné aux cycles adjacents en des positions arbitraires, et n est un entier de 2 à 4 ; dans les formules (1a) et (1b), chaque R est indépendamment un atome d'hydrogène, un groupe hydrocarboné aliphatique possédant de 1 à 10 atome(s) de carbone, un groupe hydrocarboné aromatique possédant de 6 à 18 atomes de carbone, ou un groupe hétérocyclique aromatique possédant de 3 à 17 atomes de carbone ; dans les formules (1a) et (1c), chaque Ar est indépendamment un groupe hydrocarboné aromatique possédant de 6 à 50 atomes de carbone ou un groupe hétérocyclique aromatique possédant de 3 à 50 atomes de carbone ; toutefois, au moins l'un de L et des Ar est un groupe m-valent ou monovalent formé à partir d'un composé représenté par la formule (1d) par élimination d'un atome d'hydrogène ou de plusieurs atomes d'hydrogène :
    Figure imgb0062
     dans la formule (1d), X est un groupe méthine, un atome d'azote, ou C-Ar1 et au moins l'un des X est un atome d'azote ; chaque Ar1 est indépendamment un groupe hydrocarboné aromatique possédant de 6 à 50 atomes de carbone ou un groupe hétérocyclique aromatique possédant de 3 à 50 atomes de carbone.
  2. Dispositif électroluminescent organique comme décrit dans la revendication 1, dans lequel, dans la formule générale (1), m vaut 1 ou 2.
  3. Dispositif électroluminescent organique comme décrit dans la revendication 1, dans lequel, dans la formule générale (1), n vaut 2.
  4. Dispositif électroluminescent organique comme décrit dans la revendication 2, dans lequel, dans la formule générale (1), la formule (1a) est représentée par l'une quelconque des formules (2) à (4) suivantes :
    Figure imgb0063
    Figure imgb0064
    Figure imgb0065
     dans les formules (2) à (4), Ar et R ont respectivement les mêmes significations que celles indiquées à propos des formules (1a), (1b) et (1c).
  5. Dispositif électroluminescent organique comme décrit dans la revendication 1, dans lequel la couche organique contenant un composé représenté par la formule générale (1) est une couche luminescente contenant un dopant phosphorescent.
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